in the end
by Sapphire Pirate
Summary: Jess isn't dead. Or she is, she's not really sure. All she does know is that she really needs some answers, and apparently the archangel Gabriel can give them to her. Well, she's more iffy on the archangel part. Sabriel, Destiel, and SamJess (kinda sorta all at the same time)
1. Praying's for the Smart People

In the end, it was Jess who ended up praying to Gabriel. Jess who saw how Sam had frozen when he'd seen the angel's name. Jess who felt sad when she watched Sam sometimes. Jess who was the only one who suspected something.

She chose to do it late at night, when Sam was off studying something or another or reading. Jess was outside and she prayed. "Oh, God, if thou hearest me, let me speak plainly. I wish to speak with the archangel Gabriel. I have questions, and I believe that only he, or at least he, will tell me the answers I'm looking for."

It wasn't long after that she got her response. "So, I heard you have some questions."

Jess turned around to face the angel and smiled before pausing. "Hey, Gabe." She fidgeted for a second, trying to figure out how to segway into this conversation. "I didn't actually think you were the archangel Gabriel."

Gabe - Gabriel - smiled, though Jess could tell it wasn't a real smile. It didn't quite reach his eyes. "Well, you have to admit - there were things I did that I couldn't have done if I'd been human."

She shrugged. "You never know."

He looked at her. "Questions."

Jess cleared her throat. "Right. Just - gimme a minute here, Gabe." She looked down at where she was fiddling with the hem of her shirt. "Am I dead?"

Gabriel looked up at her, surprised at the straightforwardness of her question. "Why would you think that?"

She sighed, wrapping her arms around herself. "Just answer the stupid question, Gabe. Please," she added after a moment.

The angel frowned, obviously wanting his answer first. "Not here, but yes. You're dead."

Jess nodded, feeling her eyes begin to water as the reality of her situation began to settle in. "Glad to know I was right about something." She rubbed at her eyes. "Oh, boy."

"How'd you figure it out?"

She laughed self-decrepitatingly. "Where do I start, Gabe? Dean's lonely, he only sleeps on one side of his bed - I only know cause Sam told me - and Sam swears up and down that Dean's always tried to take up as much of his bed as possible. Sam looks at me sometimes like he's not sure if I'm real or not. They're both afraid of their dad when I know he's never done anything to them. Mr. Winchester looks at his wife like she's a miracle. Sam looks at his dad sometimes and starts tearing up. There'll be a dog barking out of nowhere and Dean'll go pale like he's heard nails against a chalkboard. Sam and Dean can pick up guns, take them apart, and put them back together all within a matter of minutes. There'll be a weird news story going around and they'll think that the thing responsible isn't human." By the end of it, Jess was crying her eyes out. "And you ask me how _I_ figured it out, Gabriel? Why don't you ask me something harder - like why haven't Sam and Dean figured it out yet?"

Gabriel was quiet for a long time. "Cas asked me for a favor."

"Who the hell is Cas?"

The angel was quiet again, like he didn't want to have this conversation. Jess wrapped her arms around herself again. "Cas is my brother. He's an angel too."

Jess frowned at Gabriel, confused. "Why would it matter that he asked you for a favor?"

Gabriel sighed. "Jess, where we come from, you're dead. You died, just like Sam and Dean's mother - that's why John Winchester looks at his wife Mary like she's a miracle and why Sam looks at you like you might not be real. John raised his boys like soldiers - there's why they can take guns apart and put them back together so quickly and why they look at him like they're afraid. John died - that's why Sam cries sometimes. Dean's been to hell - the first time he went, hellhounds killed him and ever since then he's been wary of them and that's why he freaks out about the dogs. Sam and Dean hunt the supernatural and that's why they think a weird news story might have been about something that isn't human." He looked up at her. "Cas - Castiel - he was tired. So, he asked for my help. A normal life for them, Sam with you, John with Mary, and Dean with Lisa."

"Lisa and Dean broke up forever ago," Jess replied, furrowing her brow.

"I know," Gabriel replied, frowning. "Who do you think's been trying to get them back together?" He huffed out a breath, crossing his arms. "_I_ know why Dean broke up with her - doesn't mean that Cas'll believe me though. He keeps on thinking that they're going to get back together eventually." The angel looked at Jess again. "Why do you think they won't get back together?"

Jess smiled sadly. "Cause Dean doesn't love her. Sam and I had a long conversation with him after he broke up with her as to why he did it."

Gabriel half-grinned. "I'll tell you a secret - Sam from where I'm from knows too, even if he won't say anything about it. Dean and Cas are in love - it's kind of ridiculous how much they love each other. There's a huge amount of denial going around, mostly from Dean but some from Cas too, hence this favor."

The blonde nodded. "Why don't you just let Dean see Cas again and then see who Dean chooses?"  
"If my life were that easy," Gabriel muttered. He suddenly perked up. "But my life _is_ that easy." The angel looked at Jess. "What're you and Sam planning on doing tomorrow?" Jess shrugged and Gabriel grinned. "How about a walk through the city with Dean?"

Jess grinned too, her face still tear-stained and her eyes still red. "Alright, I think I can live with that."

* * *

"Hey," Jess greeted Sam when she got back to their tiny apartment.

Sam looked up, startled. "Hey. Where'd you go? I thought you were staying in tonight."

Jess shrugged. "I needed a walk to clear my head." He stood up, frowning. "What?"

"You look like you've been crying." Sam brushed Jess's hair out of her face. "Everything okay?"

She smiled at him, tired but not upset. "I'm fine, Sam. Go back to whatever you were studying. I'm gonna go shower and then go to bed." Jess went onto her tiptoes and gave Sam a peck on the lips before continuing into their bedroom. Just before she disappeared, she turned back around to where Sam was watching her. "I'm fine, really Sam." She grinned, giving him a little wave as she went into the bedroom.

Silently, Jess wondered how she had died.


	2. And We're Gonna Let It Burn

_Fire._

_Sam yelling. _

_Dean running into the room, trying to get Sam off of the bed. _

_Blood. _

_Horror in Sam's eyes. _

_Immobility._

_Pain._

_Fire._

Jess's eyes shot open as she breathed heavily, clutching her pillow. Shaking slightly, she turned to see Sam, still asleep though slightly troubled. Jess took a few deep breaths before deciding to get out of bed and walk around. _This is gonna require Gabe_, she realized as she slowly slid out of bed, taking great pains not to wake up her sleeping boyfriend. _God, he's gonna hate me for this_.

Gabriel was already there when Jess walked outside, after grabbing one of Sam's sweatshirts to wear over her pajamas. "I've got a direct line to you," he explained once she was within earshot. "Once I heard my name ping, I thought you might wanna talk to me."

She nodded, wrapping her arms around herself like she had the night before. "Were you expecting there to be nightmares?"

The angel sighed frustratedly. "You went to bed wondering about your death, didn't you?" Jess nodded guiltily. "That's the best time for your memories to creep back. Keep that in mind the next time you decide to sleep on a question involving something that's already happened." Gabriel ran his fingers through his hair, making Jess hug herself tighter, her subconscious aware of the power that ran beneath the angel's skin.

"You gonna tell me the full story now?" Gabriel looked back up at her. "Last night," Jess began, "you said that Cas asked you for a favor. I think you wouldn't have agreed to do it unless you thought it really needed to be done. So, what's the full version?"

Gabriel frowned. "It's a long story, kid."

Jess shrugged. "We've got time. Come inside?" She angled herself so that she could gesture at the door to the apartment building.

He didn't stand a chance. "Jeez, kid, don't pull out the puppy eyes. You and your boyfriend use those to your full advantage." With a grin that said she wasn't sorry at all, Jess led Gabriel into the apartment building, leaving the archangel to close the door behind himself.

Sam was awake when Jess opened the door to their apartment, her boyfriend rubbing the last remains of sleep from his eyes. "Hey," Jess greeted him, a smile blossoming on her face. "Sleep well?"

"Actually no," Sam replied, causing Jess's smile to falter a little as her own dream popped up in her mind. "I had the weirdest dream," he began, running his fingers through his hair but stopping when he saw Gabriel. "Gabe! I didn't know you were coming over." The taller brunette quickly moved to clear their tiny dining room table.

Gabriel shook his head, holding his hands up for Sam to stop. "Whoa there, Sammich. Take five and wake up before trying to take care of others." He walked inside, heading straight for Sam. When he reached the insanely tall brunette, Gabriel began to pretend-push Sam back into the bedroom. "Seriously, man. You've gotta take it easy."

The taller brunette rolled his eyes, not trying to stop Gabriel. "Alright, Gabe, I'm going. Though you won't be able to stop me from making breakfast," Sam added over his shoulder as he entered the bedroom.

When Gabriel looked back at Jess, she had a huge, bright smile on her face. "What's that for?" The angel sat himself down on one of the chairs at the table, propping his feet up on the table.

Jess shrugged, continuing to clear things from their eating area. "You like him," she said simply. "It's not everyday a person does something for their brother if they don't like the person their brother is asking a favor for." Gabriel scoffed, crossing his arms. Her smile faded as her mind drifted back to the reason Jess had called the archangel. "When you said Cas was tired, what did you mean?"

Gabriel shrugged. "He was tired of everything, of Sam and Dean's pain, of their loneliness, of the eternal bad luck." He paused, considering something. "Actually that may have been their fault a while back." The archangel looked back at Jess. "Sam and Dean broke a lot of mirrors back when they started hunting together after…" His voice drifted off, the _you died_ hanging unspoken.

"Did he get out? Of hunting I mean?" Jess cleared her throat when Gabriel just stared at her. "When Sam and I met, had Sam left hunting by then?"

"He left it when he left his father and Dean for college," Gabriel answered. Jess looked at him, clearly waiting for him to continue. "Your…death pushed him back into hunting, almost farther than he'd been before he got out."

She was quiet for a few moments before she asked, "Who did it? Killed me, I mean."

Gabriel frowned. "Jess, you know I shouldn't…"

"Okay, so, breakfast, right, Gabe?" Sam's timing couldn't have been any more fortunate for Gabriel as he walked out of the bedroom fully dressed. Jess frowned at Gabriel, her silent _We're not done talking about this_ very clear to the archangel.

"Sure, Sasquatch. Just try not to poison me again."

* * *

"A day in town with Dean? Sure, that sounds like a great idea." Sam chewed and swallowed his food before turning to Gabriel. "Dean hasn't been feeling well and I'd been trying to think of things to do to make him feel better."

Gabriel nodded, pretending to take in the information. "Huh. Well, have fun with that, you kids. My brother, or at least one of them, is in town for the day and he wanted me to show him around."

Sam nodded, chewing thoughtfully. "Alright. Maybe we'll see you today, Gabe."

The archangel exchanged a look with Jess when Sam looked down at his food. "It's always a possibility, Gigantor." He swallowed his next bite of food before pushing his chair back and standing. "Well, it's been fun, kids, but I've gotta get going."

Jess awww'ed at him and Sam looked at him, surprised. "Really? You just got here though." Sam wiped food remnants away from his mouth with his napkin before he and Jess stood in unison, completely on accident.

Gabriel shrugged. "It's just the life I lead. My brother's probably gonna have my head if I'm not at my house when he gets in. He's picky about that sort of thing." Jess rolled her eyes. _Like a guy who asked for Sam and Dean to be sent here would be picky about coming to visit his brother whom he sent to watch over them_. The archangel obviously caught the drift of Jess's thoughts from the look on her face and grinned. "See you two around."


	3. Smooth, Winchester, real smooth

"I still don't get why you dragged me into town, Sammy."

Dean was dragging his feet as he walked with Jess and Sam down the sidewalk, Jess pretending to be window-shopping while she stayed on the lookout for Gabriel and Castiel. "Because you've been grumpier than usual, Dean." The two brothers were walking slightly behind her, giving her more freedom as they stayed wrapped up in their conversation. They'd been going over it for the past ten minutes, since they got into town.

Jess turned and walked back to the two brothers, linking her arms between each of their's, walking between them. "Come on, Dean. This is supposed to be fun, remember?"

The taller blonde rolled his eyes. "That's what you said when you dragged me out of my bed this morning, yeah." He was about to continue with that line of thought but stopped short when something - or someone - caught his eye.

"See? Was that so hard to accept, De-?" Sam turned his head to reply to his brother, and, upon finding Dean distracted, then followed Dean's line of sight. Jess, noticing their silence, followed suit.

When Jess saw Castiel for the first time, she wasn't surprised at all that Dean was in love with a guy - angel - who looked - or had a vessel that looked - like that. On the other hand, Dean's taste in women became a lot clearer. "I knew there was a reason Dean chose girls who didn't understand pop culture references. Or dark hair. Or blue eyes. Or any combination thereof."

Sam looked at Jess, confused. "What?" Dean looked alarmed, staring at her long enough to convey his complete and utter horror.

Realizing she'd just spoken aloud, Jess shook her head. "Sorry, I was just thinking out loud." Then she pretended to just spot Gabriel across the street. "Hey, Gabe!" She waved a hand up in the air in an "attempt" to get the archangel's attention.

Gabriel looked up at her, a huge grin on his face. "Hey Jess!" Castiel's - Jess really hoped she wasn't wrong in assuming that the archangel's companion was Dean's Castiel - head snapped around to look at Jess, Sam, and Dean. When the dark brunette looked back at Gabriel, Jess could tell he was trying to glare holes into the archangel's head.

Sam's reaction was more that he was surprised to see Gabriel out in town rather than anything else, Jess thought. And Dean's reaction…Jess was worried they'd broken him because of how starstruck he seemed when he laid eyes on Castiel.

Jess had been worried about Gabriel's head, given that Castiel was an angel and all, but the look on his face when he looked at Dean was enough to make all of her worries to disappear for the time being. Gabriel and Castiel made their way over to the trio, Jess grinning the entire time. "Is this your brother?" Jess asked, bouncing on her toes with anticipation.

The archangel grinned. "Yeah. Cassie, these are my friends - well, Dean's not really my friend but still - Jess, Sam, and his older brother, Dean. Guys, this is my little brother Castiel." He stood patiently beside Castiel as the dark brunette and Dean continued to stare at each other. "Are you gonna shake their hands or just stare at them, Cassie?"

Castiel snapped out of his reverie, holding out a hand for Dean to shake. "It is a pleasure to meet you."

Dean shook the dark brunette's hand, still staring at him. "Uh, yeah, same to you, man." He cleared his throat, the blonde's face a shade pinker than it had been earlier. When he glanced at Jess, he could've sworn that her grin hadn't been that smug earlier. "So, what brings you into town?" Unfortunately, Dean looked at Jess again, and this time she mouthed to him, _Smooth, Winchester, real smooth_.

Gabriel answered after a few moments when Castiel was obviously having trouble coming up with an answer. "Cassie here thought it'd be fun to come and see how I was doing here in town. I decided to humor him and show him around." The archangel turned to Sam. "So you managed to get him out of the house?"

Sam smiled, a shy thing that Jess recognized from when she had first met Sam and he wasn't sure how to talk to her yet because she was incredibly pretty to her. "Yeah, well, I did promise him I'd buy lunch out. My bank account won't necessarily thank me for this trip."

Jess grinned again. "How about you and Castiel join us, Gabe? My treat," she said in answer to the sudden panicked look on Sam's face.

The archangel looked at Castiel, obviously waiting for the other to refuse the offer. Instead, Castiel nodded hesitantly, a layer of vulnerability falling over him. "Huh. Well, I guess we'll take you up on that offer, Jess."

* * *

It took them all a while to decide on a place and, when they finally had chosen and gotten themselves seated at the restaurant, approximately an hour had passed. It wasn't hard for Jess to get some alone time with Castiel. Gabriel wasn't the only one she had questions for at this point.

"So, Castiel," Jess began while Dean, Sam, and Gabriel were off ordering food for all of them and arguing over who was paying even though she had promised that she would. She made a mental note to go and end the argument before it got too bad. "I think you have something to say to Dean."

Castiel turned his stare to Jess, who smiled serenely at him. "I only met him approximately an hour ago. What could I possibly have to say to him?"

Jess shrugged. "I dunno. Maybe, 'it's good to see you again after I sent you and your brother away to live in this universe in the hopes that you'd be happy with a woman you don't love'?"

The angel's stare intensified. "Where would you come up with that idea?"

She rolled her eyes. "Does everyone seriously believe that I'm an idiot? Common fucking sense, man, seriously." The blonde leaned forwards towards Castiel. "Listen, I know that you asked Gabriel for a favor involving Dean living happily ever after with Lisa and Sam doing the same with me. The thing is, Dean doesn't love Lisa. At least, not in the way he loves you. Sure, yeah, his love with her is a really romantic love, mostly involving sex and an unhappy relationship, but it was never meant to last forever. Now, what I've heard that _you_ and Dean have, that thing is meant to last."

Castiel narrowed his eyes at Jess. "What evidence do you have to come to this conclusion?"

"The fact that Dean and Lisa aren't together anymore," Jess replied, not missing a beat. "Dean sleeps one only one side of his bed instead of the middle. He picks up women that look like you. I mean, he even briefly dated a girl named Cassandra. How much more evidence do you need?" She sighed when Castiel didn't show any signs of relenting. "Look, I'm not saying that you need to go over there and profess your undying love for him. All I'm saying is that maybe choosing to send Sam and Dean over to an alternate universe where you hope that both of them live out the rest of their lives happily wasn't necessarily the best decision at the time."

He observed her for a minute, like he was trying to read her thoughts from her face. "You are an interesting person, Jessica. I am sorry that I didn't have an earlier opportunity to acquaint myself with you." Castiel looked behind her to the line. "What are they doing?"

Jess turned around in her chair to look at the trio standing in line. "They're playing 'Rock, Paper, Scissors' to try to figure out who's gonna pay. I should probably go stop it before Dean ends up paying." She smiled back at Castiel before standing up and going over to them in order to pay for their food.


	4. Jess the Matchmaker

Their lunch went well, filled with pleasant conversation and terrible jokes (mostly from Gabriel). The way it really ended was that Sam and Castiel wandered off somewhere to discuss folklore (Sam's hobby) and Dean walked across to the street to the park in order to sit down in the grass and enjoy some peace and quiet.

"Hey," Sam said, returning to their table where they'd enjoyed their lunch in the sunshine. "I just came back to tell you that Castiel and I are gonna go wander around the plaza a little bit. We'll be back within the hour and if you're not here, we'll meet you in the park." He leaned down to kiss Jess.

She smiled, kissing Sam. "Have fun. Please don't go and buy a ton of folklore books. You know we already have a lot back home." Jess gave him a mock stern look, while Gabriel nodded, acknowledging that he'd heard both Sam and Jess and agreed with Jess's request.

Sam shrugged, smiling. "I'll try not to." Waving, he started backing away from their table before turning around and facing where he was going, back to the spot on the sidewalk where he'd left Castiel looking a little…lost.

Gabriel scoffed, watching Sam walk away. "I don't know what you see in that guy, Jess."

"Probably the same things you do," she answered, knowing she'd throw the angel off. Jess sipped innocently from her straw when Gabriel began choking on his soda. After a minute or so, he stopped coughing and glared at her.

"What. The. Fuck."

Jess grinned at Gabriel. "I'm not wrong."

"You are as far away from right as you can possibly be at this point."

She rolled her eyes at him. "Don't lie. Lying's not a good look on you." Gabriel raised an eyebrow at her. "Seriously, Gabe. I'm gone anyways. Just tell me if you slept together or anything. Tell me you've at least broached the subject with him."

"I was playing dead for a few years. Before that, I kinda made him watch Dean die. A lot. Like, over a hundred times." Jess sighed, slapping a hand to her face. "He was going to Hell! What did you expect me to do?"

"Not make him watch his big brother die over a hundred times, especially if their dad was a dick to them." She sighed again, letting her hand drop. "This is gonna be harder that I thought it was gonna be."

"I'm not gonna get together with your boyfriend in the reality where you've been dead for years," Gabriel said, like he was tired of the implication that that situation would even happen.

Jess shrugged, leaning back into her chair. "You never know, Gabe. It could happen, even after all that you put him through concerning Dean." She frowned. "Though now that I know the situation, I see how Castiel guilt-tripped you into doing this."

It was totally worth the fries to the face if she succeeded in at least planting the idea in Gabriel's head.

* * *

Jess sat down besides Dean, leaning back onto her hands to get more comfortable. "I didn't think it was that much fun, sitting on the ground." She sighed, letting herself enjoy the day for a few moments. "So, are you gonna talk to Castiel?" The punch she received on the arm closest to Dean was not unexpected. "Come on, Dean. The two of you have barely kept your eyes off of each other since you met." _Today_, she added mentally.

Dean sighed, laying down on the ground. "I don't know. I just keep getting these weird flashes and impressions of things that've never happened."

"What, like deja vu?"

"Sort of," Dean replied, Jess settling on the ground next to him. "Like I've done them, I remember doing them, except that I don't really. Like, Lisa. For some bizarre reason I have this memory of her in the hospital and then Castiel coming in and doing…something." Dean frowned, furrowing his brow. "It's a little fuzzy around the edges."

Jess nodded, her own memory/dream coming to the forefront of her mind. "I get it. But, is that a bad thing or a good thing?"

He shrugged, an impressive feat when lying down. "Both, I guess. It's not like they're all one or the other. I get impressions when I look at Castiel and this warm feeling in my chest or a cold rock in the pit of my stomach. When I look at Gabe sometimes, I just wanna punch him in the face for no good reason. I look at Sammy sometimes and I'm afraid he's gonna go off and get himself high or something. And when I look at you," Dean continued, turning his head to look at her. Jess turned her head to meet his eyes, a vague notion of what he was going through running through her mind. "I feel sorry for Sam and the irresistible urge to say I love Smurfs."

She nodded again, looking back to where Gabriel was still sitting at the table. "How good are you at keeping secrets, Dean?"

Dean let out an 'eh'. "I'm normally pretty good at keeping them. What's up?"

Jess looked at Gabriel again before turning back to Dean. "I'm pretty sure that that's actually how you and I met." Dean furrowed his eyebrows, confused. "I'm pretty sure that we met when you broke into our apartment in order to get Sam to join you on a hunt."

He held up his hands. "Whoa, hold up. What does that even mean?"

She sighed, rolling over to look at Dean again. "It means, I'm pretty sure everything around us isn't real right now."

Dean sat up. "Whoa. Start from the beginning."

Jess took a deep breath. "I'm pretty sure that we're either in a pocket dimension or something because outside of here, I'm dead and you and Sam hunt the supernatural. Castiel and Gabe are angels, and Gabe's faked his own death for a few years. Anything else?"

"Mom was killed by a demon named Azazel that we knew as the Yellow-Eyed Demon for a long time. Sam and I hunted him when we couldn't find Dad." Confused, Dean looked back at the pleased look on Jess's face as she looked at him. "What the hell did I just say?"

"That was you, making a choice." Dean and Jess turned to where Gabriel was standing over them. "I mean, you kinda coerced it out of him, Jess, but that was definitely him choosing."

She stood up, slightly relieved that the archangel wasn't yelling at her for telling Dean the truth. "Wait, so does that mean that you'll send them back?"

Gabriel took a deep breath. "I think it's not only Dean's choice at this point. I think Sam and Cassie have to choose too. Besides, Dean's choice isn't over."

Dean stared at Jess and Gabriel. "What the hell?"

The archangel rolled his eyes. "God, I forgot how thick you could be, Dean-o." He pressed two fingers to Dean's head. "Alright, so, Dean, you wanna go catch up with Samsquatch and Cassie?"

The taller man nodded, standing. "Yeah. I think Sam needs to be pulled away from all of that nerdy stuff anyway. He was the one who pulled me into town."

Jess watched as Dean started walking away. "What just happened?"

"I made him forget what I said. He remembers saying the things about his parents but not what I said about his choice." Gabriel turned back to Jess, a grin on his face. "Well, I guess we should follow him to find out what Sam and Cassie say about it." She bit her lip as Gabriel turned away. "You coming?"

She hesitated for a moment. "What if they don't choose the real world?"

Gabriel looked at her sadly. "We wait until they figure it out."


	5. In Which Cas is a Hell Raiser

Jess's mood was severely damped by her conversation with Gabriel, as was noted by the archangel by their near-silent walk to the bookstore where Sam, Dean, and Castiel currently were. "I'm sorry, Gabe. It's just that I thought everything would just be magically fixed when Dean figured out that this wasn't real."

Gabriel scoffed at her statement. "Of course this is real. It's not just a hallucination or something. It's a pocket dimension - way different from a hallucination. Trust me - Sam knows the difference between those two." He frowned when he saw the look on Jess's face. "Hey." The archangel put a hand on her arm, stopping both of them. "Listen, I know how easy you wanted this to be, and if it was that easy, then we wouldn't have been here in the first place."

She nodded, biting her lip. "Yeah, I guess you're right." Taking a deep breath, Jess put a smile back on her face. "So, to the bookstore?"

The archangel nodded. "To the bookstore."

* * *

"Took you guys long enough," Sam said when Jess and Gabriel arrived at the bookstore. "They're just staring at each other. Seriously, it's like I'm not even here."

Jess turned to Gabriel. "Were they always like that?"

Gabriel nodded. "It used to be way worse. They wouldn't even say each other. They'd just stand there and fuck each other with their eyes."

Sam nodded too. "Yeah, it was probably worse that time Castiel watched porn and ended up making out with Meg." He furrowed his eyebrows, missing Jess and Gabriel's surprised looks. "Wait, that never happened. Who's Meg?" After a moment, he shrugged it off, turning back to where Dean and Castiel were.

"Did he just say what I think he just said?" Jess stared at Dean and Castiel, her main focus on the angel.

Gabriel nodded again. "Yup. Apparently Cassie got a boner one time and made out with a demon, which doesn't really surprise me given what a _hell raiser_ he is." He grinned. "Get it? Hell raiser?" Jess shook her head, not getting the joke. The archangel sighed. "The only people who would get my joke are refusing to accept reality right now, which kind of sucks."

Jess rolled her eyes at him, a small smile on her face. "Let's just…go make sure they don't go stripping each others' clothes off in the middle of the store in their effort to get into each others' pants."

The archangel laughed, dropping an arm over Jess's shoulders, despite being a good three inches shorter than her. "I knew there was a reason I liked you, kid." They were both quiet for a few moments before Gabriel spoke up again. "Don't worry. We'll fix this."

The blonde nodded, her eyes still a little sad. "What'll we do if they don't wanna fix it?"

Gabriel grinned again. "They'll have to deal with my terrible jokes for longer than they would like to." Jess laughed at the archangel's response.

"Let's hope they wanna get it fixed then." She sighed, looking over at the trio again. "So, tell me, what's it like in reality?"

"Well, it's filled with a lot more supernatural creatures and near-world-ending disasters. And even more almost kisses between Cassie and Dean," Gabriel added. Jess nodded, waiting for the archangel to continue. "This most recent time though…"

She watched Gabriel as he seemed to remember what brought the four of them to where they currently were. "What happened, Gabriel?" Jess asked softly.

He paused for a few more moments before answering her. "Dean died again, except this time he had a bit of supernatural help that meant he didn't stay dead for too long."

"He turned into a demon," Jess said suddenly, making Gabriel look at her in surprise. "I remember, because Heaven had just gotten back under control after putting Metatron behind bars. Ash told me, sent me a message. He told me it wasn't good."

Gabriel frowned. "It was a bit more than just not good. Castiel had gotten Gadreel on his side and managed to destroy the angel tablet - the source of Metatron's extra energy - but by then, Megatron had already killed Dean."

Jess turned to look at Castiel. "It tore him apart, didn't it?"

"Cassie may have been the one to ask for this," Gabriel began, answering the question in a way. "But that doesn't mean that I didn't find Sam and Dean and ask both of them if they'd be happy with this. It was hard to get a straight answer out of Dean, but he never wanted to be a demon."

"How long?" Gabriel looked at Jess again, confused. "How long have we been here?"

The archangel turned back to the trio. "A few weeks, maybe. Not long enough to make much of a difference. Crowley's probably wondering where Dean got off to, but Dean was shaking Crowley off of his tail anyway."

Jess took a deep breath. "What would happen - if I told them?"

Gabriel shrugged. "Dean's made his choice. I'm pretty sure Sam's made his too. Now we just have to convince Cassie to make the same one."


	6. Talking Fixes Everything

Jess sat Castiel down at one of the picnic tables outside of her and Sam's apartment building. "Now, Castiel," she began, folding her hands in front of her on the table top. "Tell me everything."

Castiel looked at her. "I don't know to what you're referring."

She sighed, splaying her hands out onto the table and slumping her shoulders. "Tell me why it is you chose to have Gabriel send Sam and Dean here to live out the rest of their lives in a fantasy." Jess huffed when Castiel's expression didn't change. "September 18th, 2008. Anna Milton can hear the angels speaking to one another and Dean Winchester crawls out of a grave in a field in the middle of nowhere. Now, tell me, why do this to them?"

The angel narrowed his eyes a little, studying her. "Once again, I am sorry that I was unable to acquaint myself to you earlier in your life. It would have lead to very interesting conversations." Jess sighed, watching Castiel. "I have…made many mistakes since I met Dean and Bobby in the warehouse to which they summoned me. Although they were made with good intentions, they were mistakes nonetheless. I understood why Dean and Sam did not trust me for a very long time after them. I thought…" He paused, considering his next words. "I thought that if I were to do this one thing for them, then they would be safe from any other mistakes I might possibly make."

Jess laughed a little. "No matter where they are, it's not in their nature not to run away from danger. You know that, Castiel. Why would you try to change that?"

Castiel looked down at his hands. "Because I know how much they wanted a normal life, despite what either of them might claim." He paused for a moment. "They deserve better than what I've given them." Castiel stared at the table.

The blonde laughed abruptly, making Castiel look up at her. "I'm sorry, Castiel," she began, calming down. "But you just don't seem to get it. You gave Sam back his big brother when there was no other way for Dean to come back. You made Dean believe in himself after all his father ever did was make him think that he's worthless. And, even after every single mistake that you've made, they've let you back in, made you a part of their family." Jess sighed again, looking at Castiel sadly. "It's just…I don't know how you've managed to miss all of that, Cas."

Castiel stopped, observing Jess for a long moment. "Gabriel has explained it to you very thoroughly." She shrugged, modesty being one of her better traits.

"Listen," Jess began once Castiel hadn't said any more. "I get that this might be hard for you, but you gotta understand. It's hard for them too." She smiled a little at the angel. "Just promise me you'll think about it?" Jess stood and began to walk into the apartment building, pausing to briefly squeeze Castiel's shoulder as she passed him.

He didn't look up when Gabriel took Jess's place. "She's right, you know."

Castiel glared at the archangel. "I know that, Gabriel. But, what am I supposed to do? Leave Dean to parade around as a demon while Sam tries to find him?" He shook his head. "You've seen what's happened to Sam since Dean became a demon. It's worse than when Dean went to Hell."

Gabriel nodded, ceding to Castiel's point. "But you can't just leave them here, Castiel," the archangel said. "They're not happy. They know that this isn't right and that they belong somewhere else." He paused for a moment, studying Castiel. "That's why you did this anyway, for them to be happy, right?" Gabriel sighed when the angel didn't reply. "Castiel, listen to me. It is not your job to ensure the happiness of Sam and Dean Winchester. You should be worrying about yourself right now."

The dark brunette frowned at Gabriel. "As I told Hannah, I have already accepted my fate, Gabriel."

The archangel stared at Castiel. "And what about Sam and Dean? I know I just said you don't ensure their happiness, but, without you, they will fall apart." Castiel glared at Gabriel. "Whether you like it or not, they need you."

Castiel didn't get a chance to reply because Jess stumbled back out to where the two angels were sitting across from each other. "Guys," she said, her eyes wide. "Something's wrong."

Gabriel was the first one up, helping Jess stay standing. "What do you feel?"

Jess clutched her stomach with her free hand, the other holding on to Gabriel's shoulder. "Something's trying to pull us back. It's like this tugging feeling in my stomach. It's powerful, I can tell that much. I'm not sure how Sam and Dean are holding up." The two angels exchanged knowing looks. "You two know what's going on, don't you?"

"Now'd be a good time to call Hannah," Gabriel said, not looking at Castiel as he did, choosing to instead focus on Jess. He frowned when he could tell that his brother was actively avoiding calling the other angel. "Now, otherwise I'll get Sam or Dean to do it."

"Speak of the Devil," Jess said as the two Winchesters stumbled out of the door, similar looks of pain on their faces. "Hey guys." Sam gave Jess a strange look, and Jess felt bad momentarily, mostly for the 'speak of the Devil' comment. She gave the two brothers a weak smile, waving a hand.

The Winchesters turned their attention to Gabriel and Castiel, similar looks of realization crossing the brothers' faces. "Is it just me or did the Trickster get us again?" Dean asked, staring at Gabriel after having finally dragged his attention away from Castiel.

Gabriel clicked his tongue at Dean before looking back at Jess. "Jessie, talk to me. What does the pull feel like?"

After a moment, Jess grinned up at Gabriel. "It feels like someone's trying to write us back in." He rocked back onto his heels, a disbelieving look on his face. "Y'know, it's a shame," Jess said, turned her head back to Sam and Dean. "I never did get to read about your adventures."

"Wait," Sam began. "Are you talking about-?"

"No," Dean said. "He disappeared, remember?"

"He does that, _remember_?" Jess grinned at them. "Kill that Cain guy for me, huh, Dean? He sounds like a real dick. And tell Chuck to just ask next time," she added. "I'm pretty sure I'd just say sure to going back to reality."

That's when everything disappeared in a bright white light, like the color of grace.


	7. Let's Wrap This Up With A Bow

"I'm gonna punch him," Dean groaned, grabbing his head as he did. He sat up, fighting off the insane headache he was getting as he did. "I'm gonna punch that winged dick as many times as I can and then I'm gonna punch him again."

"Dean?" Sam wandered into the kitchen, rubbing his head. "Did what I think just happened really just happen?"

Dean grunted in affirmation. "Next time we see your boyfriend, I'm gonna punch him."

"He's not my boyfriend," the taller Winchester said immediately, though Dean gave him a disbelieving look. After a moment, Sam let out a snort. "And the next time we see _your's_, you guys need to dispense the tension and finally kiss." Dean gave Sam a sour look but didn't try to dispute his brother's statement. After all, Sam had basically had to watch as Dean and Cas practically eye-fucked each other in the middle of a bookstore in a pocket reality which probably no longer existed.

"I'm not doing it where _you_ of all people could watch," Dean said, shuddering dramatically. Sam grinned a little, pleased that Dean didn't outright deny that Cas was at least a tiny bit his boyfriend. "And what makes you think I'd tell you if we did kiss anyway?" Now, Sam's grin took up his entire face, his brother's admission making it all the better.

"Hey, guys?" Sam's glee grew, if that was possible, when he saw the absolute relief on Dean's face at the sound of Chuck's voice. "You guys okay?"

"Dean wants to punch Gabriel, so I think we're good, Chuck." Sam turned around to look at Chuck, the shorter man's concerned look not having disappeared from his face. "Speaking of Gabriel, where is he? And how is he not dead?"

Chuck waved a hand. "The details aren't really important as to how he's still alive. The important part is that he _is_ still alive and, if I'm right, should be arriving with Castiel any second now." A quiet fluttering of wings a few moments later confirmed Chuck's statement.

Castiel and Gabriel stumbled into the room, Castiel's eyes wide as he looked between Chuck to Dean to Sam. "I'm not entirely sure I'm understanding what just happened." Chuck grinned at Castiel. Dean coughed a little, a faint blush covering his cheeks. In order to save at least a shred of his dignity, he did the unwise thing and looked at Gabriel.

But, instead of the archangel grinning cheekily at him, the ex-Trickster was looking at Sam solemnly, as if he was afraid of what the taller Winchester would say to him. Chuck quickly realized that he was the fifth wheel in the room, or the third wheel to two couples as it were. He cleared his throat, suddenly aware of the sexual tension in the room. "Yeah, so, if you guys want to catch up, I'm gonna be going. Holler if you guys want to talk. Y'know, after you guys are all done making out with each other," Chuck continued, backing out of the room as quickly as he could.

Chuck's comment about making out seemed to snap everyone out of their funk. "Uh, you guys can have the kitchen," Sam said, shoving his hands into his pockets. He glanced at Gabriel once before leaving the kitchen, the archangel following a few cautious steps behind.

Castiel and Dean glanced at each other nervously before looking away again. "So," Dean began, shifting on his feet. "What just happened?"

"I'm…not sure," Castiel said, cocking his head to the side and squinting after his brother. Dean scoffed, Castiel clearly having missed Dean's change in conversational topics, and moved to sit at the kitchen table. Castiel followed shortly afterwards, still confused by Chuck's comment and Gabriel's strange behavior.

"Look, Cas," Dean began, really wishing he had a beer even though it was way too early in the morning to even be considering alcohol. "I'm pretty sure you know exactly what I'm talking about, so please, don't bullshit me." Castiel's cheeks colored suddenly, and he avoided Dean's eyes. "I'm not a demon anymore, for one. And two, I think this is a conversation that's a long time coming for both of us." Dean sighed, running a hand over his face. "Listen, Cas. I like you, a lot. And, if I'm remembering right, you really like me. So, what do you say?"

Castiel sits up straighter, meeting Dean's eyes as he throws his shoulders back. "Chuck found a way to give me back my grace, so I'm not longer in danger of dying from the influence of a grace that isn't my own." Dean looked like he really wanted to ask (which would make sense, because Dean didn't know Cas was dying) but he refrained and let Castiel continue. "If this is you suggesting you want to try to pursue a romantic, possibly sexual, relationship with me, then I agree."

* * *

Chuck was on his way back to the kitchen, having left Gabriel and Sam to their own devices, and stopped dead in his tracks at the sounds of several pots and pans clanging together. Maybe it'd be for the best if he just waited…outside the bunker. Far, far away.

* * *

Gabriel really wished that Chuck hadn't found him dying in his own little corner of the universe and brought him back to do this favor for Castiel because literally anything would be better than being stuck in a room with an awkward Sam Winchester. Okay, so the awkward part was mostly Gabriel's fault because he kinda, y'know, mentally tortured Sam and really only stopped being a dick towards the guy about five minutes ago, so Sam had good reason to not like Gabriel. But the thing was, Gabriel really liked Sam.

For some terrible reason or another, Gabriel actually liked the stupidly tall human who was supposed to be the vessel for his brother, the Devil, who actually won in a mental battle against said brother, the Devil, and overall avoided the Apocalypse. So Gabriel had a few reasons to like the kid.

But Sam hadn't punched Gabriel yet, so Gabriel took that as a good sign.

Sam flopped into an armchair in what Gabriel was assuming was the library. "Dean's right. I should want you dead for everything you've put me through." Gabriel flinched at Sam's words, but he couldn't exactly hold a grudge against the younger Winchester. He did have good reason. "But I don't," Sam continued, resting his elbows against his knees and rubbing his face with his hands.

"Don't suppose it'd help if I said I was sorry for, like, 95 percent of those things," Gabriel said flatly. His face lit up when Sam let out a laugh.

"Only 95 percent?" Sam looked up at Gabriel - and wasn't that a concept, Gabriel being taller than Sam Winchester in any situation. "What about the other 5 percent?"

Gabriel shot Sam a quick grin. "Can't say I'm sorry about the fact that it let me hang around you a little more than I was supposed to. Especially as that janitor," he added with a wink for good measure. Sam laughed again, and a little warm ball of good feelings lit up in Gabriel's chest. "Look, if you wanna take a stab at me, Sammich, go right ahead. I'm not gonna stop you, even if you are aiming to kill. Daddy knows you've got enough reason to want to maim me, just a little."

Sam rolled his eyes. "I told you, Gabriel, I don't want you dead, and I don't want you injured either. You wanna lend a helping hand? Great, fantastic. I think you've got a ways to go if you wanna learn why Jess really liked me." As soon as he finished talking, Sam's face went red, and Gabriel couldn't stop himself from grinning like a madman.

"You coming onto me, Samalam? Cause I gotta admit, I've always had a soft spot for the fiery types. You remember Kali, don't you? Man, what a woman." Gabriel went dreamy eyed for a second before looking at Sam again, worried he'd crossed a line.

But Sam was smiling and shaking his head like he was _fond_ of Gabriel, for Dad's sake. Maybe Gabriel had a shot with Sam after all.

Now if they could just convince Dean and Cassie to get out of the kitchen. (Gabriel had seen that pantry. He wanted sweets like four hours ago.)

* * *

In the end, it was really thanks to Jess that all of this even happened.


End file.
